"We have become great mates and I can honestly say that there has not been one cross word said between us during that time," says Stephenson.
It was also a night run that provided the inspiration for the Great Kauri Run. The Coromandel Golf Club greenkeeper says the "moments of magic" often happen when he and Andy are running together.
"We are at our creative best when we are running. The ideas just seem to flow when you are in that free headspace. There is something about being out there in the elements and pushing your body that seems to give the mind real clarity."
Stephenson and Reid wanted to organise a running event that would "put the Coromandel back on the map" and give back by replanting kauri trees across the peninsula.
Locals, with help and inspiration from others, came up with the idea that for every competitor who entered the Great Cranleigh Kauri Run, organisers would plant a new kauri.
The idea and the event, with the help of Stephenson's wife Rita, who is a key part of the operation, took off. After this year's 11th event, which is scheduled for next Saturday, they will have planted more than 3000 trees.
"It's great," said Stephenson. "It is amazing to think that number of kauri trees have been planted during that time and now there is an avenue of kauri that will hopefully be there forever."
New Zealand had "only 1 per cent of the original kauri trees left ... we are obviously keen to change that".
The vision is to plant 10,000 trees over the next 10 years and to create an avenue of kauri all the way from Waikawau to Coromandel.
As the kauri have grown in number so too have the athletes. In a poll run by the popular Running Skirt Shop, runners voted the Great Cranleigh Kauri Run the North Island's best run and New Zealand's second best run.
The organisers expect more than 300 entries next weekend and runners are coming from as far afield as California, Hawaii, French Polynesia and Australia.
Stephenson says the Great Kauri Run is well respected by elite runners and weekend warriors nationwide.
"It is one of those runs that has wow factor at every turn," he said. "But at the same time it is a real test and I don't think there are many runners who can complete the 32km race without having to stop to take breath and walk for a bit."
The Great Kauri Run begins at Waikawau Beach on the rugged Pacific coast, then traverses the Coromandel Range to finish at Coromandel Town on the Hauraki Gulf.
Along the way competitors experience native bush and stream crossings while climbing to more than 800m. And much of the course is on private land, which means competitors get to see parts of the Coromandel not typically open to the public.
Asked what advice he would offer newcomers to the race, Stephenson laughs. "What can I tell people that will mean they still come to the race? It is tough going but a real adventure on some land you only have access to once a year. I would recommend that you pace yourself and enjoy how beautiful the Coromandel is."
Course records for this scenic but savage challenge belong to Galatea's Sjors Corporaal (2:25.35, 2009) and Australian Hanny Allston (2:42.11, 2008). Favourites this year include Kauri Run legend Colin Earwaker.
The 55-year-old Rotorua runner was the race's first winner in 2004, and is the only person to have participated in all 11 years. But even more impressively, he has only once finished outside the top five. Last year he was a strong fifth.
The traditional 32km Classic is the feature event, but in recent years organisers have introduced 13km, 21km and 76km options.
"We wanted the event to be more inclusive across all types of runners and walkers," says Stephenson.
"The 13km Kauri Crossing is a great introduction to trail running and is actually the most popular option. The 21km Demi-Marathon is a good step up to completing the feature 32km Kauri Classic. And for a few true endurance junkies, the 76km Kauri Ultra is one of New Zealand's premier ultra-distance challenges."
Speaking of long-distance challenges, Stephenson isn't done with pushing himself to the limit just yet, even though he is approaching 70.
The veteran has his heart set on completing an ironman before he hangs up the running shoes.
"It's something I have always wanted to do and it is still on the bucket list," he said. "I don't have too many more years when it will be possible so I need to get cracking on that one. I wonder if there is an age limit for that. I reckon I could still do it."
Stephenson is a salt of the earth character who people love to support and follow. He is content that the legacy of the Kauri Run will also live on.
"We have some great people in the community here that are really engaged with the ethos of this event. We know that they will continue this tradition and make a real difference to the Coromandel. We thank every competitor who has run or walked in this event, they are the ones who have helped make it happen."
And that legacy began because of a chance conversation over a run on a cold night on the country roads of the Coromandel.
The run
When: Saturday, November 22
Where: Coromandel. The run begins at Waikawau Beach, then traverses the Coromandel Ranges to finish at Coromandel township on the Hauraki Gulf.
Event options: 13km, 21km, 32km classic and 76km ultra
For more information visit: http://www.arcevents.co.nz/kaurirun/